Herein, we have undertaken the synthesis and reactivity of a 6-membered saturated NHC borane aduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I2 led to NHC...
The NHC•borane chemistry has been majorly restricted to imidazol-2-ylidene classes of carbenes. In our previous communication, we have reported the synthesis of 6-SIDipp•BH3 [6-SIDipp = 1,3-di(2,6-diisopropylphenyl) tetrahydropyrimidine-2-ylidene] and its electrophilic...
Compounds
of boranes with N-heterocyclic carbenes are known, yet
little attention has been paid to NHC compounds of boron bearing methyl
and halogen moieties together. The reason can be attributed to the
hazardous methyldichloroborane (MeBCl2), which ignites
in air. We describe here convenient solution-phase access to SIDipp·MeBCl2 (SIDipp = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene)
(3) by a salt metathesis reaction of SIDipp·BCl3 (2) with MeLi. Replacement of the chlorine atoms
of 3 with stepwise addition of AgOTf led to the formation
of SIDipp·MeBCl(OTf) (4) and SIDipp·MeB(OTf)2 (5). In the case of 4, all of the
substituents on the boron atom are different. Subsequently, we extended
our synthetic approach to the amidinate system and prepared PhC(NtBu)2B(Me)Cl (7) from the reaction
of PhC(NtBu)2BCl2 (6) with MeLi.
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